Ethyl orthoformate → HCID 67972043, compound

HRID 713711Notes

Reaction equation

[NH2:1][CH:2]1[CH:7]2[CH:3]1[CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6]2.[CH2:15](OC(OCC)OCC)C.[N-:25]=[N+:26]=[N-:27].[Na+]>C(O)(=O)C>[N:1]1([CH:2]2[CH:7]3[CH:3]2[CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6]3)[CH:15]=[N:27][N:26]=[N:25]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of tert-butyl 6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate (7.3 g, 25.3 mmol) and triethylorthoformate (24 mL, 152 mmol) in acetic acid (200 mL) was added sodium azide (9.9 g, 152 mmol) and the resulting mixture was set under inert atmosphere. The mixture was heated at 100° C. for 4 h and then cooled to RT at which time the volatiles were removed in vacuo. The residue was taken up in ethyl acetate (200 mL) and washed with aqueous sodium bicarbonate solution, followed by brine. The organics were dried over sodium sulfate, filtered, and concentrate to dryness under vacuum. The residue was placed in the refrigerator overnight and the next day a solid white precipitate was observed. The precipitate was triturated with hexane and the solvent was carefully decanted to give the title compound 3.2 g (50.3%) as a white solid. ESI-MS calculated for C11H17N5O2: Exact Mass: 251.28. Found 252.28.

Workup

temperaturecooled to RT at which time the volatiles
customwere removed in vacuo
washwashed with aqueous sodium bicarbonate solution
dry with materialThe organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrate to dryness under vacuum
customwas placed in the refrigerator overnight
customThe precipitate was triturated with hexane
customthe solvent was carefully decanted

Sources & evidence

ORD record: ord-68a2d9fae7bc4f8ebe6ccf1e73ae4b9a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09186354B2

Reaction notes

Loading…